Hydrochloric Acid → HCID 69411401, compound

Participants

Reaction Steps

Methanesulfonyl chloride (0.09 mL, 1.2 mmol) was added to a solution of phenethyl alcohol (0.14 mL, 1.2 mmol) and triethylamine (0.21 mL, 1.5 mmol) in acetonitrile (5 ml) at room temperature. The mixture was stirred for 1 hour, and then (2,2,4,6,7-pentamethyl-3-pyrrolidinyl-2,3-dihydro-1-benzofuran-5-yl)piperazine obtained in Example 134 (343 mg, 1 mmol) was added. After stirring for 16 hours at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified with basic silica gel column chromatography (ethyl acetate/hexan=4/1) to obtain 166 mg as a free base. The free base was treated with 4N hydrogenchloride in ethyl acetate to obtain 96 mg (yield 18%) of the title compound. mp. 176–180° C. (decomposition) (ethanol-ethyl acetate).

Provenance & Evidence